Meet the Team James Gilbert, Captive & Large Client Relationship Manager

I started in the City quite young. I wasn’t particularly suited to a traditional academic route, so I decided to explore opportunities in London. After several interviews, I secured a role at Sphere Drake Insurance Limited as an underwriting assistant in the marine and aviation reinsurance XOL team.

It was very much an entry‑level position, covering typical office junior responsibilities, but it gave me a strong grounding in how the market operates. You learn quickly at that level how underwriting decisions are made, how brokers interact with the market, and how risk is assessed in practice.

That early exposure was important. It gave me a clear understanding of the fundamentals and, just as importantly, introduced me to the pace and culture of the City. I was commuting in, learning on the job, and building relationships from the outset. That combination of hands‑on experience and market exposure is what has kept me in the industry.

My current role sits within the multinational team and focuses on large client relationships and captives. It is relatively new, as I moved into the role earlier this year.

Before that, I spent three years in a business development position at Starr, working across London and Europe. That involved building relationships, expanding share of wallet across product lines, and focusing on key clients. Through that work, I became more closely involved in captives, which is an area Starr has developed strongly in the US and is now building further in the UK and Europe.

In my current role, the focus is on deepening those relationships and understanding how we can support clients more effectively over the long term. That means taking a more holistic view of their business, how they structure risk, how captives might fit into that, and where Starr can add value, whether through broader line participation, balance sheet support or more strategic input.

I’ve been at Starr for over 15 years, and a big part of what’s kept me here is the journey, the growth, and the sense that we’re building for the long term. We’re privately owned rather than publicly listed, which creates a slightly different dynamic, and it suits the way we think about developing the business.

It’s also been exciting to see Starr expand its footprint over the years, and more recently to be part of Starr’s first acquisition, bringing IQUW into the business. That’s a significant step, and it broadens what we can do as a platform.

For me, the differentiator is quality and speed of service, with quick turnaround times and fast decision-making. Starr operates with a relatively flat structure, without layers of red tape, which means we can move quickly and provide brokers and clients with clarity.

As the business has grown, and with the acquisition bringing additional capability, it has become easier to have broader, more joined-up conversations with clients and brokers. The breadth of our offering has increased, but the underlying approach remains the same. We focus on responsiveness, decisiveness, and a consistent level of service.

One of the biggest changes for me recently has been moving back into a team environment after working more independently for three years. It’s different, and I’m still getting used to it, but it’s a good balance. I’m meeting new people, understanding how they operate, and building relationships across functions, not only with underwriters, but with the wider team that supports large clients and captives.

Part of how I work is very simple. I walk the floor regularly to stay connected, make sure people know who I am, and understand what underwriters are looking for so I can support them more effectively. .

From my perspective, the major development is the expansion of the captive market in the UK and Europe. Starr’s US business has built this strongly over the past five to ten years, and in the UK, there is a clear opportunity to grow, particularly with changes expected in the UK regime in 2027, which should create more scope for captives.

I am also interested in how captives are starting to play in more specialised lines. Property and casualty will always be central because of scale, but there is growing interest in areas such as cyber, renewables, and motor. These are more specialised areas, and they are where captives are beginning to build activity. Because Starr has underwriting expertise across those lines, it puts us in a strong position to support that evolution.

Put yourself out there early when it comes to relationships and don’t ‘burn your bridges’!Build them from the start and do not focus too narrowly on one line of business. Learn as much as you can across the market, as the broader your understanding, the more valuable you become.

I would also focus on skills that make a difference throughout a career, such as presentation skills, negotiation skills, and emotional intelligence. How you come across, internally and externally, matters. Having empathy is important too, being able to put yourself in other people’s shoes and recognise that it is not just about you.

Self-awareness is part of that. I have benefited from coaches and people who have guided me over the years, both inside and outside the market, and it is something I would encourage others to invest in early.

I’m excited about building out Starr’s captive capability further in the UK and Europe, getting to know new and existing captives, strengthening relationships with captive managers, and growing Starr’s role as a partner providing balance sheet protection. It will not happen overnight, but it is a space with a strong long-term future.

There is also a significant focus on planning and communication. I am keen to ensure the proposition is clear internally with underwriters and externally with clients as we engage with new captive opportunities and the large client fraternity. We are not starting from scratch, but the runway is significant, and there is real scope to build something meaningful if we do it properly and lean on the experience of Starr’s US peers.